Head to Head includes singles and doubles results.
| 05/16/24 | Leonard Chinchay over Felipe Montoya | 6-2; 7-5 | Playoff Match |
| 11/10/23 | Felipe Montoya over Leonard Chinchay | 6-2; 6-3 | |
| 04/24/23 | Leonard Chinchay over Felipe Montoya |
7-6; 2-6; TB 10-1 |
|
| 11/23/22 | Leonard Chinchay over Felipe Montoya |
6-2; 4-6; TB 10-8 |
|
| 04/10/22 | Leonard Chinchay over Felipe Montoya |
7-6; 1-6; TB 10-5 |
|
| 01/28/22 | Leonard Chinchay over Felipe Montoya | 7-6; 6-3 |
